Tip
Chip Conley talks about product decisions at Airbnb: “The two sharing economy darlings were Uber and Airbnb. Uber was pretty much a mobile-only app. Airbnb started as non-mobile then went mobile. Then it was like, ‘Oh, wouldn’t it be interesting if everything was mobile?’ At some point, I just said, ‘Listen, let’s get some older people who are hosts in here to see how well they will be versed in managing their listing purely on mobile.’ I was a voice for older users, in this case hosts, that was helpful to engineers and designers and product managers in their twenties.”
Turns out AI product assumptions work the same way.
Your product team wants to ship a conversational AI interface—chat-only, no traditional UI, just talk to the AI naturally. The demo looks incredible. Engineers love it. It’s faster to build. Uber proved mobile-only works. Why maintain legacy interfaces?
But your users aren’t all 25-year-old engineers. You’re serving procurement managers at manufacturing companies. IT directors at hospitals. Finance teams at law firms. These are people in their 40s, 50s, 60s who’ve used ERP systems for 20 years. They’re comfortable with structured forms, dropdown menus, clear workflows. A purely conversational interface might intimidate them or slow them down.
Younger product managers see “chat is the future” and assume everyone will adapt. They design for themselves. You know better. You’ve watched enough product decisions over decades fail because they optimized for the builders, not the buyers. You remember when enterprise software tried to force mobile-first on desktop power users. You remember when “consumerization of IT” meant stripping out features executives actually needed.
The pattern: teams build for the loud, technical early adopters, not the quiet majority who pay the bills. You can see the demographic mismatch before it hits the metrics. Your buyers are 20 years older than your builders. What feels intuitive to a 28-year-old engineer might feel alien to a 52-year-old CFO.
This recognition—knowing when product assumptions miss key user segments—comes from enough years to personally span the demographic gap. You remember what interfaces felt like before you became technical. You can simulate the perspective of users who aren’t digital natives. That empathy lets you advocate for design decisions that actually convert buyers, not just impress peers.
Context
Chip Conley joined Airbnb at 52, reporting to Brian Chesky (age 31). When the product team considered going mobile-only like Uber, Chip pointed out that hosts (average age 10+ years older than guests) needed desktop interfaces to manage listings.
He was the voice for older users in a room of 20-something builders. For experienced executives managing AI product decisions, this demographic awareness is critical—you personally remember not being a digital native, can anticipate what intimidates older users, and recognize when teams are optimizing for builders instead of buyers.
That perspective only comes from spanning the generational gap yourself.